Ethylene Oxide → HCID 18995664, compound

Participants

Reaction Steps

A solution of N,N-bis(phenylmethyl)-1-ethoxymethyl-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine (1.7 g, 3.9 mmole, Example 1 Part E) in tetrahydrofuran (50 mL) was cooled to -78° C. Butyllithium (1.6 mL of 2.5M in hexanes, 4.1 mmole) was added dropwise and the reaction mixture was stirred for 5 minutes. Ethylene oxide was run over the surface of the reaction mixture. After 10 minutes the reaction mixture was allowed to warm to ambient temperature. The ethylene oxide addition was stopped when the reaction temperature reached 0° C. The reaction was quenched with diethyl ether and water. The ether layer was separated, dried over magnesium sulfate and then concentrated under vacuum. The resulting residue was purified by column chromatography (silica gel eluting with 5-10% ethyl acetate in methylene chloride v/v) to provide 1.4 g of N,N-bis(phenylmethyl)-2-(3-hydroxypropyl)-1-ethoxymethyl-1H-imidazo[4,5-c]quinolin-4-amine.

Provenance & Evidence